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Introduction to
Organic Chemistry
F I F T H E d iti o n
Introduction to
Organic Chemistry
F I F T H E d iti o n
W i l l i a m H . B r ow n T ho m a s P oo n
Beloit College Claremont McKenna College
Scripps College
Pitzer College
J o h n W i l ey & S o ns, I n c .
Vp & Publisher: Kaye Pace
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978-1118-083383
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10 9 8 7 6 5 4 3 2 1
To Carolyn,
with whom life is a joy
Bill Brown
To Sophia,
sky, fish, fireworks
Thomas Poon
A b o u t th e A u t h o r s
William H. Brown is Professor Emeritus at Beloit College, where he was twice

named Teacher of the Year. He is also the author of two other college textbooks: Organic
Chemistry 5/e, coauthored with Chris Foote, Brent Iverson, and Eric Anslyn, published in
2009, and General, Organic, and Biochemistry 9/e, coauthored with Fred Bettelheim, Mary
Campbell, and Shawn Farrell, published in 2010. He received his Ph.D. from Columbia
University under the direction of Gilbert Stork and did postdoctoral work at California
Institute of Technology and the University of Arizona. Twice he was Director of a Beloit
College World Affairs Center seminar at the University of Glasgow, Scotland. In 1999, he
retired from Beloit College to devote more time to writing and development of educational
materials. Although officially retired, he continues to teach Special Topics in Organic Syn-
thesis on a yearly basis.
Bill and his wife Carolyn enjoy hiking in the canyon country of the Southwest. In ad-
dition, they both enjoy quilting and quilts.
Thomas Poon is Professor of Chemistry in the W.M. Keck Science Department of

Claremont McKenna, Pitzer, and Scripps Colleges, three of the five undergraduate institu-
tions that make up the Claremont Colleges in Claremont, California. He received his B.S.
degree from Fairfield University (CT) and his Ph.D. from the University of California, Los
Angeles under the direction of Christopher S. Foote. Poon was a Camille and Henry Drey-
fus Postdoctoral Fellow under Bradford P. Mundy at Colby College (ME) before joining the
faculty at Randolph-Macon College (VA) where he received the Thomas Branch Award for
Excellence in Teaching in 1999. He was a visiting scholar at Columbia University (NY) in
2002 (and again in 2004) where he worked on projects in both research and education with
his friend and mentor, Nicholas J. Turro. He has taught organic chemistry, forensic chem-
istry, upper-level courses in advanced laboratory techniques, and a first-year seminar class
titled Science of Identity. His favorite activity is working alongside undergraduates in the
laboratory on research problems involving the investigation of synthetic methodology in
zeolites, zeolite photochemistry, natural products isolation, and reactions of singlet oxygen.
When not in the lab, he likes to play guitar and sing chemistry songs to his daughter
Sophie.
vii
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C o n t e n ts O v e r v i e w
01 Covalent Bonding and

Shapes of Molecules 1 12 Aldehydes and Ketones 416
02 Acids and Bases 41

13 Carboxylic Acids 457
03 Alkanes and Cycloalkanes 63

14 Functional Derivatives of
Carboxylic Acids 488
04 Alkenes and Alkynes 108

15 Enolate Anions 526
05 Reactions of Alkenes and Alkynes 129

16 Organic Polymer Chemistry 564
06 Chirality: The Handedness

of Molecules 167 17 Carbohydrates 586
07 Haloalkanes 200
18 Amino Acids and Proteins 619
08 Alcohols, Ethers, and Thiols 239

19 Lipids 649
09 Benzene and Its Derivatives 282

20 Nucleic Acids (Online Chapter) 674
10 Amines 331
21 The Organic Chemistry
of Metabolism (Online Chapter) 700
11 Spectroscopy 361
ix
Con tents
01 Covalent Bonding and Summary of Key Questions 57

Shapes of Molecules 1 Quick Quiz 58
Key Reactions 59
1.1 How Do We Describe the Electronic Problems 59
Structure of Atoms? 2 Looking Ahead 62
1.2 What Is the Lewis Model of Bonding? 5 Group Learning Activities 62
1.3 How Do We Predict Bond Angles and the
Shapes of Molecules? 14
1.4 How Do We Predict If a Molecule Is
Polar or Nonpolar? 18
03
1.5 What Is Resonance? 19
Alkanes and Cycloalkanes 63
1.6 What Is the Orbital Overlap Model of
Covalent Bonding? 22
1.7 What Are Functional Groups? 28
3.1 What Are Alkanes? 64
Summary of Key Questions 32
3.2 What Is Constitutional Isomerism in
Quick Quiz 34 Alkanes? 66
Problems 35 3.3 How Do We Name Alkanes? 69
Looking Ahead 40 3.4 What Are Cycloalkanes? 73
Group Learning Activities 40 3.5 What Is the IUPAC System of
C H E MI C AL C O NN E C T I O NS Nomenclature? 75
1A Buckyball: A New Form of Carbon 17 3.6 What Are the Conformations of Alkanes and
Cycloalkanes? 76
3.7 What Is Cis–Trans Isomerism in
Cycloalkanes? 83
3.8 What Are the Physical Properties of Alkanes
02 Acids and Bases 41 and Cycloalkanes? 87

3.9 What Are the Characteristic Reactions of
Alkanes? 91
3.10 What Are the Sources of Alkanes? 91
2.1 What Are Arrhenius Acids and
Bases? 42 Summary of Key Questions 94
2.2 What Are Brønsted–Lowry Acids and Quick Quiz 96

Bases? 43 Key Reactions 97
2.3 How Do We Measure the Strength of an Problems 97
Acid or Base? 46 Looking Ahead 102
2.4 How Do We Determine the Group Learning Activities 104
Position of Equilibrium in an
Putting It Together 104
Acid–Base Reaction? 48
2.5 What Are the Relationships C H E MI C AL C O NN E C T I O NS
between Acidity and Molecular 3A The Poisonous Puffer Fish 84
Structure? 50 3B Octane Rating: What Those Numbers at the
2.6 What Are Lewis Acids and Bases? 54 Pump Mean 94
x
co n te n t s xi
04 Alkenes and Alkynes 108 Looking Ahead 165

Group Learning Activities 166
C H E MI C AL C O NN E C T I O NS
4.1 What Are the Structures and Shapes 5A Catalytic Cracking and the Importance of
of Alkenes and Alkynes? 110 Alkenes 133
4.2 How Do We Name Alkenes and Alkynes? 112
4.3 What Are the Physical Properties
of Alkenes and Alkynes? 120
06
4.4 Why Are 1-Alkynes (Terminal Alkynes) Chirality: The Handedness
Weak Acids? 122 of Molecules 167
Quick Quiz 124
6.1 What Are Stereoisomers? 168
Problems 124
6.2 What Are Enantiomers? 169
Looking Ahead 128
6.3 How Do We Designate the Configuration
Group Learning Activities 128 of a Stereocenter? 173
C H E MI C AL C O NN E C T I O NS 6.4 What Is the 2n Rule? 176
4A Ethylene, a Plant Growth 6.5 How Do We Describe the Chirality of Cyclic
Regulator 109 Molecules with Two Stereocenters? 180
4B Cis–Trans Isomerism in Vision 111 6.6 How Do We Describe the Chirality
4C Why Plants Emit Isoprene 121 of Molecules with Three or More
Stereocenters? 182
6.7 What Are the Properties of
Stereoisomers? 183
6.8 How Is Chirality Detected in the
05
Laboratory? 184
Reactions of Alkenes and
Alkynes 129 6.9 What Is the Significance of Chirality
in the Biological World? 185
6.10 How Can Enantiomers Be Resolved? 186
5.1 What Are the Characteristic Reactions of
Alkenes? 130
Quick Quiz 190
5.2 What Is a Reaction Mechanism? 130
Problems 191
5.3 What Are the Mechanisms of
Electrophilic Additions to Alkenes? 136 Chemical Transformations 195
5.4 What Are Carbocation Looking Ahead 196
Rearrangements? 147 Group Learning Activities 196
5.5 What Is Hydroboration–Oxidation of Putting It Together 196
an Alkene? 150
5.6 How Can an Alkene Be Reduced to an
6A Chiral Drugs 187
Alkane? 153
5.7 How Can an Acetylide Anion Be
Used to Create a New Carbon–Carbon
Bond? 155
5.8 How Can Alkynes Be Reduced to Alkenes
and Alkanes? 157
Quick Quiz 159
07
7.1
Haloalkanes 200
How Are Haloalkanes Named? 201

Key Reactions 160 7.2 What Are the Characteristic Reactions
Problems 161 of Haloalkanes? 203
xii co n te n t s
7.3 What Are the Products of Nucleophilic C H E MI C AL C O NN E C T I O NS

Aliphatic Substitution Reactions? 206 8A Nitroglycerin: An Explosive and a Drug 243
7.4 What Are the SN2 and SN1 Mechanisms 8B Blood Alcohol Screening 260
for Nucleophilic Substitution? 208
8C Ethylene Oxide: A Chemical Sterilant 268
7.5 What Determines Whether SN1
or SN2 Predominates? 211
7.6 How Can SN1 and SN2 Be Predicted Based
09
on Experimental Conditions? 217 Benzene and
7.7 What Are the Products of Its Derivatives 282
b-Elimination? 219
7.8 What Are the E1 and E2 Mechanisms
9.1 What Is the Structure of Benzene? 283
for b-Elimination? 222
9.2 What Is Aromaticity? 286
7.9 When Do Nucleophilic Substitution
and b-Elimination Compete? 225 9.3 How Are Benzene Compounds Named, and
What Are Their Physical Properties? 289
9.4 What Is the Benzylic Position, and How Does
Quick Quiz 230
It Contribute to Benzene Reactivity? 292
Key Reactions 231
9.5 What Is Electrophilic Aromatic
Problems 231 Substitution? 295
Chemical Transformations 236 9.6 What Is the Mechanism of Electrophilic
Looking Ahead 237 Aromatic Substitution? 296
Group Learning Activities 238 9.7 How Do Existing Substituents on
Benzene Affect Electrophilic Aromatic
Substitution? 305
7A The Environmental Impact
9.8 What Are Phenols? 314
of Chlorofluorocarbons 204
7B The Effect of Chlorofluorocarbon
Legislation on Asthma Sufferers 228 Quick Quiz 322
Key Reactions 322
Problems 324
Chemical Transformations 329
08 8.1
Alcohols, Ethers,
and Thiols 239
What Are Alcohols? 240

Looking Ahead 330
9A Carcinogenic Polynuclear Aromatics and
8.2 What Are the Characteristic Cancer 293
Reactions of Alcohols? 246
9B Capsaicin, for Those Who Like It Hot 318
8.3 What Are Ethers? 260
8.4 What Are Epoxides? 264
8.5 What Are Thiols? 268
10
8.6 What Are the Characteristic Reactions Amines 331
of Thiols? 271
Quick Quiz 274
10.1 What Are Amines? 333
Key Reactions 274
10.2 How Are Amines Named? 334
Problems 275
10.3 What Are the Characteristic Physical
Chemical Transformations 279 Properties of Amines? 337
Looking Ahead 280 10.4 What Are the Acid–Base Properties of
Group Learning Activities 281 Amines? 340
co n te n t s xiii
10.5 What Are the Reactions of Amines with C H E MI C AL C O NN E C T I O NS
Acids? 344 11A Infrared Spectroscopy: A Window on Brain
10.6 How Are Arylamines Synthesized? 346 Activity 368
10.7 How Do Amines Act as Nucleophiles? 347 11B Magnetic Resonance Imaging 391
Quick Quiz 350
12
Key Reactions 350 Aldehydes and Ketones 416
Problems 351
Looking Ahead 357 12.1 What Are Aldehydes and Ketones? 417
Group Learning Activities 357 12.2 How Are Aldehydes and Ketones
Putting It Together 357 Named? 417
12.3 What Are the Physical Properties of
Aldehydes and Ketones? 421
10A Morphine as a Clue in the Design and
Discovery of Drugs 332 12.4 What Is the Most Common Reaction Theme
of Aldehydes and Ketones? 422
10B The Poison Dart Frogs of South America:
Lethal Amines 338 12.5 What Are Grignard Reagents, and How
Do They React with Aldehydes and
Ketones? 423
12.6 What Are Hemiacetals and Acetals? 427
11
12.7 How Do Aldehydes and Ketones React
Spectroscopy 361 with Ammonia and Amines? 434
12.8 What Is Keto–Enol Tautomerism? 437
12.9 How Are Aldehydes and Ketones
11.1 What Is Electromagnetic Radiation? 362 Oxidized? 441
11.2 What Is Molecular Spectroscopy? 364 12.10 How Are Aldehydes and Ketones
11.3 What Is Infrared Spectroscopy? 364 Reduced? 443
11.4 How Do We Interpret Infrared Spectra? 367 Summary of Key Questions 445
11.5 What Is Nuclear Magnetic Resonance? 378 Quick Quiz 447
11.6 What Is Shielding? 380 Key Reactions 447
11.7 What Is an NMR Spectrum? 380 Problems 448
11.8 How Many Resonance Signals Chemical Transformations 454
Will a Compound Yield in Its NMR Spectroscopy 455
Spectrum? 382
Looking Ahead 456
11.9 What Is Signal Integration? 385
11.10 What Is Chemical Shift? 386
11.11 What Is Signal Splitting? 388
12A A Green Synthesis of Adipic Acid 442
11.12 What Is 13C-NMR Spectroscopy, and
How Does It Differ from 1H-NMR
Spectroscopy? 391
13 Carboxylic Acids 457

11.13 How Do We Solve an NMR
Problem? 394
Quick Quiz 400 13.1 What Are Carboxylic Acids? 458
Problems 401 13.2 How Are Carboxylic Acids Named? 458
Looking Ahead 414 13.3 What Are the Physical Properties
Group Learning Activities 415 of Carboxylic Acids? 461
xiv co n te n t s
13.4 What Are the Acid–Base Properties C H E MI C AL C O NN E C T I O NS

of Carboxylic Acids? 462 14A Ultraviolet Sunscreens and Sunblocks 490
13.5 How Are Carboxyl Groups Reduced? 466 14B From Moldy Clover to a Blood Thinner 491
13.6 What Is Fischer Esterification? 470 14C The Penicillins and Cephalosporins:
13.7 What Are Acid Chlorides? 473 b-Lactam Antibiotics 492
13.8 What Is Decarboxylation? 475 14D The Pyrethrins: Natural Insecticides of
Summary of Key Questions 479 Plant Origin 503
Quick Quiz 480 14E Systematic Acquired Resistance in Plants 506
Key Reactions 480

Problems 481
15
Enolate Anions 526
Looking Ahead 487
C H E MI C AL C O NN E C T I O NS 15.1 What Are Enolate Anions, and How
13A From Willow Bark to Aspirin and Beyond 466 Are They Formed? 527
13B Esters as Flavoring Agents 472 15.2 What Is the Aldol Reaction? 530
13C Ketone Bodies and Diabetes 476 15.3 What Are the Claisen and Dieckmann
Condensations? 537
15.4 How Are Aldol Reactions and Claisen
Condensations Involved in Biological
14
Processes? 545
Functional Derivatives of
15.5 What Is the Michael Reaction? 547
Carboxylic Acids 488
Quick Quiz 554
14.1 What Are Some Derivatives of Carboxylic
Acids, and How Are They Named? 489 Key Reactions 555
14.2 What Are the Characteristic Reactions of Problems 556

Carboxylic Acid Derivatives? 495 Chemical Transformations 561
14.3 What Is Hydrolysis? 496 Looking Ahead 562
14.4 How Do Carboxylic Acid Derivatives Group Learning Activities 563
React with Alcohols? 501
14.5 How Do Carboxylic Acid Derivatives React
15A Drugs That Lower Plasma Levels of
with Ammonia and Amines? 503
Cholesterol 546
14.6 How Can Functional Derivatives of
15B Antitumor Compounds: The Michael
Carboxylic Acids Be Interconverted? 505
Reaction in Nature 553
14.7 How Do Esters React with Grignard
Reagents? 507
14.8 How Are Derivatives of Carboxylic Acids
16
Reduced? 509
Organic Polymer
Chemistry 564
Quick Quiz 514
Key Reactions 515
16.1 What Is the Architecture of Polymers? 565
Problems 516
16.2 How Do We Name and Show the Structure
Chemical Transformations 522 of a Polymer? 565
Looking Ahead 523 16.3 What Is Polymer Morphology? Crystalline
Group Learning Activities 523 versus Amorphous Materials 567
Putting It Together 523 16.4 What Is Step-Growth Polymerization? 568
co n te n t s xv
16.5 What Are Chain-Growth Polymers? 573 18.3 What Are the Acid–Base Properties of
16.6 What Plastics Are Currently Recycled Amino Acids? 623
in Large Quantities? 579 18.4 What Are Polypeptides and Proteins? 630
Summary of Key Questions 580 18.5 What Is the Primary Structure of a
Quick Quiz 581 Polypeptide or Protein? 631
Key Reactions 582 18.6 What Are the Three-Dimensional Shapes

of Polypeptides and Proteins? 635
Problems 582
Looking Ahead 584
Quick Quiz 643
Key Reactions 644
Problems 645
16A Stitches That Dissolve 573
Looking Ahead 648
16B Paper or Plastic? 575
17
17.1
Carbohydrates
What Are Carbohydrates?

586
586
18A Spider Silk: A Chemical and Engineering
Wonder of Nature 640
19
17.2 What Are Monosaccharides? 587 Lipids 649
17.3 What Are the Cyclic Structures
of Monosaccharides? 591
17.4 What Are the Characteristic Reactions
19.1 What Are Triglycerides? 650
of Monosaccharides? 596
19.2 What Are Soaps and Detergents? 653
17.5 What Are Disaccharides and
Oligosaccharides? 601 19.3 What Are Phospholipids? 655
17.6 What Are Polysaccharides? 604 19.4 What Are Steroids? 657
Summary of Key Questions 606 19.5 What Are Prostaglandins? 662
Quick Quiz 608 19.6 What Are Fat-Soluble Vitamins? 665
Key Reactions 608 Summary of Key Questions 668
Problems 609 Quick Quiz 669
Looking Ahead 614 Problems 669
Group Learning Activities 614 Looking Ahead 672
Putting It Together 615 Group Learning Activities 673
C H E MI C AL C O NN E C T I O NS C H E MI C AL C O NN E C T I O NS
17A Relative Sweetness of Carbohydrate 19A Snake Venom Phospholipases 657

and Artificial Sweeteners 602 19B Nonsteroidal Estrogen Antagonists 661
17B A, B, AB, and O Blood-Group
Substances 603
18 Amino Acids and

Proteins 619 20
20.1
Nucleic Acids
(Online Chapter)
What Are Nucleosides and

674
18.1 What Are the Many Functions of Nucleotides? 675

Proteins? 620 20.2 What Is the Structure of DNA? 678
18.2 What Are Amino Acids? 620 20.3 What Are Ribonucleic Acids (RNA)? 685
xvi co n te n t s
20.4 What Is the Genetic Code? 687 21.5 What Are the Reactions of the b-Oxidation
20.5 How Is DNA Sequenced? 689 of Fatty Acids? 713
Summary of Key Questions 694 21.6 What Are the Reactions of the Citric Acid
Cycle? 717
Quick Quiz 696
Problems 696
Quick Quiz 721
Key Reactions 722
Problems 722
20A The Search for Antiviral Drugs 677
20B DNA Fingerprinting 694
Appendix 1 cid Ionization Constants

A
21
The Organic Chemistry of for the Major Classes of
Metabolism Organic Acids A.1
(Online Chapter) 700 Appendix 2 haracteristic 1H-NMR Chemical
C
Shifts A.2
21.1 What Are the Key Participants in Appendix 3 haracteristic 13C-NMR Chemical
C
Glycolysis, the b-Oxidation of Fatty Acids, Shifts A.3
and the Citric Acid Cycle? 701 Appendix 4 Characteristic Infrared Absorption
21.2 What Is Glycolysis? 706 Frequencies A.4
21.3 What Are the Ten Reactions of Glossary G.1

Glycolysis? 707 Answers Section Ans.1
21.4 What Are the Fates of Pyruvate? 711 Index I.1
P r e face
Goals of This Text

This text is designed for an introductory course in organic chemistry and assumes, as background, a
prior course of general chemistry. Both its form and content have been shaped by our experiences in
the classroom and by our assessment of the present and future direction of the brief organic course.
A brief course in organic chemistry must achieve several goals. First, most students who elect
this course are oriented toward careers in science, but few if any intend to become professional
chemists; rather, they are preparing for careers in areas that require a grounding in the essentials of
organic chemistry. Here is the place to examine the structure, properties, and reactions of rather sim-
ple molecules. Students can then build on this knowledge in later course work and professional life.
Second, an introductory course must portray something of the scope and content of organic
chemistry as well as its tremendous impact on the ways we live and work. To do this, we have in-
cluded specific examples of pharmaceuticals, plastics, soaps and detergents, natural and synthetic
textile fibers, petroleum refining, petrochemicals, pesticides, artificial flavoring agents, chemical
ecology, and so on at appropriate points in the text.
Third, a brief course must convince students that organic chemistry is more than just a catalog
of names and reactions. There are certain organizing themes or principles, which not only make the
discipline easier to understand, but also provide a way to analyze new chemistry. The relationship
between molecular structure and chemical reactivity is one such theme. Electronic theory of organic
chemistry, including Lewis structures, atomic orbitals, the hybridization of atomic orbitals, and the
theory of resonance are presented in Chapter 1. Chapter 2 explores the relationship between molecu-
lar structure and one chemical property, namely, acidity and basicity. Variations in acidity and basic-
ity among organic compounds are correlated using the concepts of electronegativity, the inductive
effect, and resonance. These same concepts are used throughout the text in discussions of molecular
structure and chemical reactivity. Stereochemistry is a second theme that recurs throughout the text.
The concept and importance of the spatial arrangement of atoms is introduced in Chapter 3 with the
concept of conformations in alkanes and cycloalkane, followed by cis/trans isomerism in Chapters 3
(in cycloalkanes) and 4 (in alkenes). Molecular symmetry and asymmetry, enantiomers and absolute
configuration, and the significance of asymmetry in the biological world are discussed in Chapter 6.
The concept of a mechanistic understanding of the reactions of organic substances is a third major
theme. Reaction mechanisms are first presented in Chapter 5; they not only help to minimize mem-
ory work but also provide a satisfaction that comes from an understanding of the molecular logic that
governs how and why organic reactions occur as they do. In this chapter we present a set of five fun-
damental patterns that are foundational to the molecular logic of organic reactions. An understand-
ing and application of these patterns will not only help to minimize memory work but also provide
a satisfaction that comes from an understanding of how and why organic reactions occur as they do.
The Audience
This book provides an introduction to organic chemistry for students who intend to pursue
careers in the sciences and who require a grounding in organic chemistry. For this reason, we make
a special effort throughout to show the interrelation between organic chemistry and other areas of
science, particularly the biological and health sciences. While studying with this book, we hope
that students will see that organic chemistry is a tool for these many disciplines, and that organic
compounds, both natural and synthetic, are all around them—in pharmaceuticals, plastics, fibers,
agrochemicals, surface coatings, toiletry preparations and cosmetics, food additives, adhesives,
xvii
5.3 What Are the Mechanisms of Electrophilic Additions to Alkenes? 137
xviii P r ef a ce
S T R AT E g Y
Use Markovnikov’s rule, which predicts that H adds to the least substituted carbon of the double bond and halogen adds to
the more substituted carbon.
and elastomers. Furthermore, we hope that students will recognize that organic chemistry is a
SOLUTION
dynamic and ever-expanding area ofthescience waiting openly for those who are prepared, both by
hydrogen of
CH 3 HCl is added to
training
ƒ and an inquisitive nature, to this
askcarbon
questions and explore.
(a) CH 3CCH 3 (b) Cl
ƒ
I
CH3
New to This Edition
2-Iodo-2-methylpropane
1-Chloro-1-methylcyclopentane See problems 5.17–5.20, 5.28
p●r “Mechanism”
● o b l E m 5.2boxes have been added for each mechanism in the book. These Mecha-
nism boxes serve as road maps and are a new way of presenting mechanisms using basic
Name and draw a structural formula for the major product of each alkene addition reaction:
steps and recurring themes that are common to most organic reaction mechanisms. This
(a) CH approach
3CH “ CH 2 a+llows
HI ¡students to(b)see that reactions CH2+HI have ¡ many steps in common, and it makes
the reactions easier to understand and remember. By graphically highlighting the mecha-
nisms in
Chemists the for
account text, we emphasize
the addition of HX to anthe importance
alkene of mechanisms
by a two-step mechanism, which for learning organic chem-
sitry,byand
we illustrate mechanisms
the reaction of 2-buteneare
witheasier
hydrogenfor the students
chloride to locateLetquickly.
to give 2-chlorobutane. us
first look at this two-step mechanism in general and then go back and study each step in detail.
Mechanism
electrophilic addition of hCl to 2-Butene
STEp 1: Add a proton. The reaction begins with the transfer of a proton from HCl to 2-butene, as shown
by the two curved arrows on the left side of Step 1:
slow, rate H
d+ d- determining + ƒ -
⁄
CH3CH “ CHCH 3 + H ¬ Cl CH3C H ¬ CHCH3 + Cl

⁄
(a nucleophile) (an electrophile) sec-Butyl cation

(a 2° carbocation
intermediate)
The first curved arrow shows the breaking of the pi bond of the alkene and its electron pair now
forming a new covalent bond with the hydrogen atom of HCl. In this step, the carbon–carbon
double bond of the alkene is the nucleophile (the electron-rich, nucleus-seeking species) and
HCl is the electrophile (the electron-poor, electron-seeking species). The second curved arrow
shows the breaking of the polar covalent bond in HCl and this electron pair being given entirely
to chlorine, forming chloride ion. Step 1 in this mechanism results in the formation of an organic
cation and chloride ion.
STEp 2: Reaction of an electrophile and a nucleophile to form a new covalent bond. The reaction of the
sec-butyl cation (an electrophile and a Lewis acid) with chloride ion (a nucleophile and a Lewis
base) completes the valence shell of carbon and gives 2-chlorobutane:
Cl
- + fast ƒ
Cl + CH3C HCH2CH3 " CH3CHCH 2CH3
Chloride ion sec -Butyl cation 2-Chlorobutane
(a Lewis base) (a Lewis acid)
(a nucleophile) (an electrophile)
●● New “Group Learning Activities” appear with the end-of-chapter problems, and provide
students with the opportunity to learn organic chemistry collaboratively. This will encourage
Brown_c05_129-166hr.indd 137 8/7/12 2:27 PM
students to work in groups and foster more active learning in their studying.
G R O U P L E A R N I N G AC T I V I T I E S
5.55 Take turns quizzing each other on the reactions 5.56 Using a piece of paper or, preferably, a whiteboard
presented in this chapter in the following ways: or chalkboard, take turns drawing the mechanisms
(a) Say the name of a reaction and ask each other of each reaction in this chapter from memory. If you
to come up with the reagents and products of forget a step or make a mistake, another member of
that reaction. For example, if you say “catalytic the group should step in and finish it.
hydrogenation of an alkene” the answer should 5.57 With the exception of ethylene to ethanol, the acid-
be “H2/Pt reacts to give an alkane.” catalyzed hydration of alkenes cannot be used for the
(b) Describe a set of reagents and ask each other synthesis of primary alcohols. Explain why this is so.
what functional group(s) the reagents react
with. For example, if you say “H2/Pt,” the
answer should be “alkenes” and “alkynes.”
(c) Name a functional group or class of compound
as a product of a reaction and ask what func-
tional group or class of compound could be
used to synthesize that product. For example,
if you say “alkene,” the answer should be
“alkyne.”
Visit https://textbookfull.com
now to explore a rich
collection of eBooks, textbook
and enjoy exciting offers!
P r ef a ce xix
●● Due to overwhelming demand, we have combined the chapters on organic spectroscopic tech-
niques into one chapter, Chapter 11, while still providing a sound conceptual treatise on
organic spectroscopy. In combining the chapters, students are shown that the absorption of
electromagnetic radiation and transitions between energy states are common themes to both
infrared spectroscopy and NMR spectroscopy.
●● “Key Terms and Concepts” now appear within the “Summary of Key Questions.” In doing
so, we shift the emphasis from simply memorizing a list of terms to seeing the terms (high-
lighted in bold) in the context of important conceptual questions.
●● We have reduced the length of the text. Using reviewer input and feedback from instructors
who have used the text, we removed material that we identified as being less important to our
audience’s learning of organic chemistry. We also moved some chapters online, to the text
website and to WileyPLUS. The result is a manageable amount of material that still provides
a thorough introduction to organic chemistry. Chapter 20, Nucleic Acids, and Chapter 21,
The Organic Chemistry of Metabolism, will be available in WileyPLUS and at the text website:
www.wiley.com/college/brown.
Special Features
“How To” Boxes: Have your students ever wished for an easy-to-follow, step-by-step guide to
understanding a problem or concept? We have identified topics in nearly every chapter that often
give students a difficult time and created step-by-step How To guides for approaching them.
Draw Mechanisms
Mechanisms show how bonds are broken Correct use of curved arrows...
and formed. Although individual atoms H H
H -
HOW TO 5.1
H Br≠ + ≠Br≠
may change positions in a reaction, the +
≠ ≠
≠ ≠
curved arrows used in a mechanism are H +

H
only for the purpose of showing electron H H
movement. Therefore, it is important to Incorrect use of curved arrows...
remember that curved arrow notation
always shows the arrow originating from H H
H -
H Br≠ + + ≠Br≠
≠ ≠
≠ ≠
a bond or from an unshared electron pair

H + H
(not the other way around).
H H
a common mistake is to use curved arrows to indicate

the movement of atoms rather than electrons
Chemical Connection Boxes include applications of organic chemistry to the world around
us, particularly to the biochemical, health, and biological sciences. The topics covered in
these boxes represent real-world applications of organic chemistry and highlight the relevance
between organic chemistry and the students’ future careers.
“Putting It Together” Cumulative Review Questions: In this text, end-of-chapter problems are
organized by section, allowing students to easily refer back to the chapter if difficulties arise. This
way of organizing practice problems is very useful for learning new material. Wouldn’t it be help-
ful for students to know whether they could do a problem that wasn’t categorized for them (i.e., to
know whether they could recognize that problem in a different context, such as an exam setting)?
To help students in this regard, we have added a section called Putting It Together (PIT) at the end
of Chapters 3, 6, 10, 14, and 17. Each PIT section is structured much like an exam would be or-
ganized, with questions of varying type (multiple choice, short answer, naming, mechanism prob-
lems, predict the products, synthesis problems, etc.) and difficulty (often requiring knowledge of
concepts from two or more previous chapters). Students’ performance on the PIT questions will
xx P r ef a ce
aid them in assessing their knowledge of the concepts from these groupings of chapters. The solu-
tions to the Putting It Together questions appear in the Student Solutions Manual.
Problem-Solving Strategies: One of the greatest difficulties students often encounter when
attempting to solve problems is knowing where to begin. To help students overcome this chal-
lenge, we include a Strategy step for every worked example in the text. The strategy step will help
students to determine the starting point for each of the example problems. Once students are
familiar with the strategy, they can apply it to all problems of that type.
EXAMPLE 5.5
Draw a structural formula for the product of the acid-catalyzed hydration of 1-methylcyclohexene.
S T R AT E G Y
Use Markovnikov’s rule, which states that the H adds to the carbon of the carbon–carbon double bond bearing the greater
number of hydrogens and that OH adds to the carbon bearing the lesser number of hydrogens.
SOLUTION
CH3
CH3
H2SO4
+H2O OH
1-Methylcyclohexene 1-Methylcyclohexanol
See problems 5.19, 5.20, 5.28, 5.32
Quick Quizzes: Research on reading comprehension has shown that good readers self-monitor
their understanding of what they have just read. We have provided a tool that will allow students
to do this, called the Quick Quiz. Quick quizzes are a set of true or false questions at the end
of every chapter designed to test students’ understanding of the basic concepts presented in the
chapter. The questions are not designed to be an indicator of their readiness for an exam. Rather,
they are provided for students to assess whether they have the bare minimum of knowledge needed
QUICK QUIZ
Answer true or false to the following questions to assess your general knowledge of the concepts in this chapter. If
you have difficulty with any of them, you should review the appropriate section in the chapter (shown in parenthe-
ses) before attempting the more challenging end-of-chapter problems.
1. Catalytic reduction of an alkene is syn stereoselective. 13. Hydroboration of an alkene is regioselective and stereo-
(5.6) selective. (5.5)
2. Borane, BH3, is a Lewis acid. (5.5) 14. According to the mechanism given in the text for acid-
3. All electrophiles are positively charged. (5.3) catalyzed hydration of an alkene, the H and OH
groups added to the double bond both arise from the
4. Catalytic hydrogenation of cyclohexene gives hexane.
same molecule of H2O. (5.3)
(5.6)
15. Acid-catalyzed addition of H2O to an alkene is called
5. A rearrangement will occur in the reaction of 2-methyl-
hydration. (5.3)
2-pentene with HBr. (5.4)
16. If a compound fails to react with Br2, it is unlikely that the
6. All nucleophiles are negatively charged. (5.3) compound contains a carbon–carbon double bond. (5.3)
7. In hydroboration, BH3 behaves as an electrophile. (5.5) 17. Addition of Br2 and Cl2 to cyclohexene is anti-stereo-
8. In catalytic hydrogenation of an alkene, the reducing selective. (5.3)
agent is the transition metal catalyst. (5.6) 18. A carbocation is a carbon that has four bonds to it and
9. Alkene addition reactions involve breaking a pi bond bears a positive charge. (5.3)
and forming two new sigma bonds in its place. (5.3) 19. The geometry about the positively charged carbon of a
10. The foundation for Markovnikov’s rule is the relative carbocation is best described as trigonal planar. (5.3)
stability of carbocation intermediates. (5.3) 20. The carbocation derived by proton transfer to ethylene
11. Acid-catalyzed hydration of an alkene is regioselective. is CH3CH2 . (5.3)
(5.3) 21. Alkyl carbocations are stabilized by the electron-with-
12. The mechanism for addition of HBr to an alkene involves drawing inductive effect of the positively charged car-
one transition state and two reactive intermediates. (5.3) bon of the carbocation. (5.3)
P r ef a ce xxi
to begin approaching the end-of-chapter problems. The answers to the quizzes are provided at the
bottom of the page, so that students can quickly check their progress, and if necessary, return to
the appropriate section in the chapter to review the material.
More Practice Problems: It is widely agreed that one of the best ways to learn the material in
organic chemistry is to have students do as many of the practice problems available as possible. We
have increased the number of practice problems in the text by 15%, providing students with even
more opportunities to learn the material. For example, we’ve included a section called Chemical
Transformations in nearly every chapter, which will help students to familiarize themselves with
the reactions covered both in that chapter and in previous chapters. These problems provide a
constructivist approach to learning organic chemistry. That is, they illustrate how concepts con-
stantly build on each other throughout the course.
Organic Synthesis: In this text, we treat organic synthesis and all of the challenges it presents
as a teaching tool. We recognize that the majority of students taking this course are intending to
pursue careers in the health and biological sciences, and that very few intend to become synthetic
organic chemists. We also recognize that what organic chemists do best is to synthesize new com-
pounds; that is, they make things. Furthermore, we recognize that one of the keys to mastering
organic chemistry is extensive problem solving. To this end, we have developed a large number
of synthetic problems in which the target molecule is one with an applied, real-world use. Our
purpose in this regard is to provide drills in recognizing and using particular reactions within
the context of real syntheses. It is not our intent, for example, that students be able to propose a
synthesis for procaine (Novocaine), but rather that when they are given an outline of the steps by
which it can be made, they can supply necessary reagents.
Greater Attention to Visual Learning: Research in knowledge and cognition has shown that vi-
sualization and organization can greatly enhance learning. We have increased the number of call-
outs (short dialog bubbles) to highlight important features of many of the illustrations throughout
the text. This places most of the important information in one location. When students try to
recall a concept or attempt to solve a problem, we hope that they will try to visualize the relevant
illustration from the text. They may be pleasantly surprised to find that the visual cues provided
by the callouts help them to remember the content as well as the context of the illustration.
this carbon forms the

bond to hydrogen
CH3 CH3 CH3

Cl
CH3C CH2 H Cl CH3CHCH2 CH3CHCH2Cl
2-Methylpropene Isobutyl cation 1-Chloro-2-methylpropane
(a 1° carbocation) (not formed)
CH3 CH3 CH3

this carbon forms Cl
the bond to CH3C CH2 H Cl CH3CCH3 CH3CCH3
hydrogen
Cl
2-Methylpropene tert -Butyl cation 2-Chloro-2-methylpropane
(a 3° carbocation) (product formed)
Organization: An Overview
Chapters 1–10 begin a study of organic compounds by first reviewing the fundamentals of
covalent bonding, the shapes of molecules, and acid–base chemistry. The structures and typical
reactions of several important classes of organic compounds are then discussed: alkanes, alkenes
and alkynes, haloalkanes, alcohols and ethers, benzene and its derivatives, and amines, aldehydes,
and ketones, and finally carboxylic acids and their derivatives.
xxii P r ef a ce
Chapter 11 introduces IR spectroscopy, and 1H-NMR and 13C-NMR spectroscopy.

Discussion of spectroscopy requires no more background than what students receive in general
chemistry. The chapter is freestanding and can be taken up in any order appropriate to a par-
ticular course.
Chapters 12–16 continue the study of organic compounds, including aldehydes and
ketones, carboxylic acids, and finally carboxylic acids and their derivatives. Chapter 15 concludes
with an introduction to the aldol, Claisen, and Michael reactions, all three of which are important
means for the formation of new carbon–carbon bonds. Chapter 16 provides a brief introduction
to organic polymer chemistry.
Chapters 17–20 present an introduction to the organic chemistry of carbohydrates, amino
acids and proteins, nucleic acids, and lipids. Chapter 21, The Organic Chemistry of Metabo-
lism, demonstrates how the chemistry developed to this point can be applied to an understand-
ing of three major metabolic pathways—glycolysis, the b-oxidation of fatty acids, and the citric
acid cycle.
WileyPLUS for Organic Chemistry—A Powerful

Teaching and Learning Solution
WileyPLUS is an innovative, research-based online environment for effective teaching and

learning.
WileyPLUS builds students’ confidence because it takes the guesswork out of studying by provid-
ing students with a clear road map: what they should do, how they should do it, and if they did it right.
This interactive approach focuses on:
CONFIDENCE: Research shows that students experience a great deal of anxiety over studying.
That’s why we provide a structured learning environment that helps students focus on what to
do, along with the support of immediate resources.
MOTIVATION: To increase and sustain motivation throughout the semester, WileyPLUS helps
students learn how to do it at a pace that’s right for them. Our integrated resources—available
24/7—function like a personal tutor, directly addressing each student’s demonstrated needs with
specific problem-solving techniques.
SUCCESS: WileyPLUS helps to ensure that each study session has a positive outcome by putting
students in control. Through instant feedback and study objective reports, students know if they
did it right, and where to focus next, so they achieve the strongest results.
With WileyPLUS, our efficacy research shows that students improve their outcomes by as
much as one letter grade. WileyPLUS helps students take more initiative, so you’ll have greater
impact on their achievement in the classroom and beyond.
Four unique silos of assessment are available to instructors for creating online homework
and quizzes and are designed to enable and support problem-solving skill development and con-
ceptual understanding:
Reaction Explorer—Students’ ability to understand mechanisms and predict synthesis reactions

greatly impacts their level of success in the course. Reaction Explorer is an interactive system
for learning and practicing reactions, syntheses, and mechanisms in organic chemistry with
P r ef a ce xxiii
advanced support for the automatic generation of random problems and curved arrow mechanism
diagrams.
Mechanism Explorer provides valuable practice of reactions and mechanisms:
Synthesis Explorer provides meaningful practice of single and multistep synthesis:
End-of-Chapter Problems—A subset of the end-of-chapter problems is included for use in

WileyPLUS. Many of the problems are algorithmic and feature structure drawing/assessment
functionality using MarvinSketch, with immediate answer feedback.
Prebuilt Concept Mastery Assignments—Students must continuously practice and work
organic chemistry problems in order to master the concepts and skills presented in the course.
Prebuilt concept mastery assignments offer students ample opportunities for practice in each
chapter. Each assignment is organized by topic and features feedback for incorrect answers.
These assignments pull from a unique database of over 25,000 questions, over half of which
require students to draw a structure using MarvinSketch.
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tressolennelement parle de ce qu’il voult dire et par moult
55 beaux termes et vers gracieux bien leonimez; ne mieulx ne
pourroit estre dit plus soubtilment, ne par plus mesurez
trais,
de ce qu’il voult traictier.
Mais en accordant a l’oppinion, a laquelle contredisés sans
faille a mon auis, trop traicte deshonnestement en aucunes
60 pars, et meismement ou parçonnage que il claime Raison,
laquelle nomme les secrez membres plainement par nom.
Et ad ce que son oppinion soustenez, et communiquez que
ainsi doye raisonnablement estre fait, et alegués que es
choses
que Dieu a faictes, n’a nulle laidure, et par consequent n’en
65 doit le nom estre eschiué. Je dis et confesse que voirement
crea Dieu toutes choses pures et nettes venans de soy;
n’adonc
en l’estat d’innocence ne eust esté laidure les nommer; mais
par la polucion de pechié deuint homme immonde, dont
encore
nous est demouré pechié originel, ce tesmoingne l’escripture
70 sainte. Si comme par comparaison puis alleguer: Dieux fist
Lucifer bel sur tous angelz, et lui donna nom tressolennel et
bel, qui puis fu par son pechié ramené a orrible laidece par
quoy le nom, tout soit il de soy tres bel, si donne il orreur
aux
oyans pour l’impression de la personne.
75 Encore proposez que Jhesucrist en parlant des
pecherresses
les appella meretrix, etc. Et que il les appellast [fol. 89
verso a] par cellui non, vous puis souldre que cellui nom
de meretrix n’est mie deshonneste a nommer selon la vilté
de la
chose; et plus vilment pourroit estre dit meismes en latin; et
que
80 honte doie estre deboutee en parlant en publique des
choses
dont nature mesmes se hontoie. Je dis que (sauue la
reuerence
de l’aucteur et la vostre) grant tort commettez contre
la noble vertu de honte, qui de sa nature reffraint les
goliardises
et deshonnestetez en diz et fais; et que ce soit grant
85 vice et hors ordre de policie honneste et de bonnes meurs
appert en mains lieux de l’escripture saincte; et que ne doye
estre repudié le nom ne que se[s] reliques fussent
nommées.
Je vous confesse que le nom ne fait la deshonnesteté de la
chose,
mais la chose fait le nom deshonneste. Pour ce selon mon
90 foible auis en doit estre parlé sobrement, et non sans
necessité
pour fin d’aucun cas particulier comme de maladie ou aultre
honnesteté necessaire. Et si comme naturelment les
mucierent
noz premiers parens, deuons faire en fait et en parole.
Et encore ne me puis taire de ce dont trop sui mal content,
95 que l’office de Raison, laquelle il mesmes dit fille de Dieu,
doie mettre auant telle parole et par maniere de prouerbe,
comme ie ay nottee en ycellui chapittre la ou elle dit a
l’Amant
que en la guerre amoureuse vault mieulz deceuoir que
deceu
estre.[31] Et vrayement je ose dire que la Raison, maistre
100 Jehan de Meun, renia son pere a celluy mot; car trop donna
autre doctrine. Et que mieulx vaulsist l’un que l’autre,
s’ensuiuroit
que tous deux fussent bons, qui ne puet estre. Et je
tiens par oppinion contraire que moins est [fol. 89 verso b]
mal, a royalment parler,[32] estre deceu que deceuoir.
105 OR ALONS OULTRE en considerant la matiere ou
maniere
de parler qui au bon auis de pluseurs fait a reprochier.
Beau Sire Dieux! quel orribleté! quel deshonnesteté! et
diuers reprouués enseignemens recordé ou chapitre de la
Vieille. Mais pour Dieu, qui y pourra notter fors enortemens
110 sophistes tous plains de laidure et toute vilaine memoire?
Ha!
hay! entre vous qui belles filles auez et bien les desirez
entroduire
a vie honneste, bailliez leur, bailliez et querez le Romant
de la Rose pour apprendre a discerner le bien du mal—que
dis ie—mais le mal du bien! Et a quel utilité ne a quoy
profite
115 aux oyans ouir tant de laidures?
Puis ou chapitre de Jalousie, pour Dieu, quelz grans biens
y peuent estre nottez? n’a quel besoing recorder les
deshonnestetez
et laides paroles, qui assez sont communes en la bouche
des maleureux passionez d’ycelle maladie? Quel bon
exemple
120 ne entroduction puet estre ce? Et la laidure, qui la est
recordee
des femmes! Dient pluseurs en lui excusant que ce
est le Jaloux qui parle, et voirement fait ainsi comme Dieu,
qui
parla par la bouche Jeremie. Mais sans faille quelsque
adicions mençongeuses qu’il ait adioustees, ne peuent
(Dieux
125 mercis) en riens amenrir ne rendre empirees les condicions
des
femmes. Ha! Hay! et quant il me souuient des faintises,
Faulz Semblans, et choses dissimulees en mariage et autre
estat que l’en peut retenir d’ycellui traictié—certes je juge
que moult sont beaulx et proffitables recors a ouir! [fol. 90
a].
130 Mais le personnage qu’il appelle le prestre Genius dit
merueilles! Sans doubte les œuures de nature fussent ja
pieça
du tout faillies, se il tant ne les eust recommandees. Mais
pour Dieu! qui est cil qui me sceust declairier ou souldre a
quoy peut estre proffitable le grant procés plein de vitupere,
135 qu’il appelle Sermon comme par derrision de saincte
predicacion,
qu’il dit que fait cellui Genius, ou tant a de deshonnestetez
et de noms et moz sophistes trouuez plus atisans les
secrez de nature, lesquelz doiuent estre teus et non
nommez?
Et puis que point ne voit on descontinuer l’euure qui par
140 ordre commun faillir ne puet; car se autrement fust, bon
seroit pour le proffit de generacion humaine trouer et dire
moz
et termes atisans et enflamans pour inanimer homme a
continuer
l’œuure. Encore plus fist l’aucteur, (se bien en ay
memoire) dont trop ne me puis merueillier a quel fin. Car ou
145 dit sermon il ioint auec en maniere de figure paradis et les
joyes qui la sont. Bien dit que en cellui yront les vertueux;
et puis conclut que tous entendent, hommes et femmes
sans
espargnier, a perfurnir et exerciter les œuures de nature; ne
en ce ne fait excepcion de loy, comme se il voulsist dire,
mais
150 dit plainement que ilz seront sauuez. Et par ce semble que
maintenir vueille le pechié de luxure estre nul, ains vertu,
qui
est erreur et contre la loy de Dieu. Ha! quel semence et
quel doctrine! quans grans biens en peuent ensuiuir! Je croy
que mains en ont laissié le monde, et entrés en religion, ou
155 deuenus hermites pour celle saincte lecture, [fol. 90 b] ou
retrais
de male vie et esté sauuez de tel enortement, qui sans
faille oncques ne vint, dire l’ose a qui qu’il desplaise, fors
de courage corrompu et abandonné a dissolucion et vice,
qui peut estre cause de grant inconuenient et pechié.
160 ET ENCORE pour Dieu, REGARDONS OULTRE un
petit, en quelle maniere puet estre valable et a bonne fin ce
que tant et si excessiuement, impetueusement, et
tresnonveritablement
il accuse, blasme, et diffame femmes de pluseurs
tresgrans vices, et leurs meurs tesmoingne estre pleins de
toute
165 peruersité, et par tant de repliques et aucques en tous
parçonnages
ne s’en puet saouler? Car se dire me voulez que ce face
le Jaloux comme passioné, ie ne sçay entendre qu’il
apertiengne
a l’office de Genius, qui tant recommande et enorte que
l’en couche auecques elles sans delaissier l’œuure qu’il tant
170 loue. Et cil mesmes dit sur tous parçonnages moult de grans
vituperes d’elles; et dit de fait, fuiés, fuiez, fuiez le serpent
venimeux;[33] et puis si dit que on les continue sans
delaissier.
Cy a malement grant contradicion de commander a fuir ce
que il veult que on suiue, et suiuir ce que il veult que on
fuie,
175 mais puis que tant sont peruerses, ne les deust commander
approchier aucunement; car qui inconuenient redoubte,
eschiuer le doit. Et pour ce que il tant deffent dire son secret
a femme, qui du sauoir est si engrant, comme il recorde, [34]
dont
iene scay ou tous les deables trouua tant de fatras et de
paroles
180 gastees, qui la sont arrengees par long procés. Mais je
pry tous ceulx, qui tant le font autentique et tant y
adioustent
foy, qu’ilz [fol. 90 verso a] me sachent a dire quans ont veus
accusez, mors, pendus, ou reprochiez en rue par
l’encusement
de leurs femmes? Si croy que cler les trouueront semees.
185 Non obstant que bon conseil seroit et louable que un
chascun
tenist son secret clos pour le plus seur, car de toute gent est
il devicieux. Et n’a pas moult comme ouy raconter que un
fu accusez et puis pendus par soy estre descouuert a un
sien
compere, en qui se fioit; mais ie croy que en la face de
iustice
190 pou vont les clameurs ne les plaintes de tant orribles maulz,
des grans desloyaultez et des grans deableries que il dit que
tant malicieusement et secretement sceuent femmes
commettre.
Si est voirement bien secret, quant il n’appert a
nullui. Et comme autrefois ay dit sur ceste matiere en un
195 mien dictié appellé l’Epistre au Dieu d’Amours, ou sont les
contrees ou les royaumes qui par leurs grans iniquitez sont
exillés?[35] Mais, sans parler a volenté, disons de quelz grans
crismes peut on accuser meismes les pires et qui plus
deçoiuent?
Que peuent elles faire, de quoy te deçoiuent? Se elles te
demandent
200 de l’argent de ta bourse, dont ne le t’emblent ou
tollent elles pas; ne leur bailles mie, se tu ne veulz. Et se tu
dis que tu en es assotés, si ne t’en assotes pas. Te vont elles
en ton hostel querir, prier, ou prendre a force? Bon seroit
sauoir comment elles te deçoiuent. Et encore tant
superfluement
205 et laidement parla des femmes mariees, qui si deçoiuent
leurs maris, duquel estat ne pot sauoir par experience et
tant en parla generaument. A quelle bonne fin pot ce estre,
ne quel bien [fol. 90 verso b.] ensuiure, n’y sçay entendre
fors empeschement de bien et de paix de mariage, et rendre
210 les maris qui tant oyent babuises et fatras, se foy y
adioustent,
souspeçonneux et pou amans leurs femmes. Dieux quelle
exortacion! comme elle est proffitable! Mais vraiement
puisque
en general ainsi toutes blasma, de croire par ceste raison
suis contrainte, que oncques n’ot acointance ne hantise de
215 femme honnourable ne vertueuse; mais par pluseurs
femmes
dissolues et de male vie hanter (comme font communement
les
luxurieux) cuida ou faingny sauoir que toutes telles fussent;
car d’aultres n’auoit cognoiscence. Et se seulement eust
blasmé les deshonestes et conseillié elles fuir, bon
enseignement
220 et iuste seroit; mais non, ains sans excepcion toutes
les accuse. Mais se tant oultre les mettes de raison se
chargia
l’aucteur d’elles accuser ou iugier non veritablement, blasme
aucun n’en doit estre imputé a elles, mais a cellui qui si loins
de verité dist la mençonge, qui n’est mie creable comme le
225 contraire appere (sic) manifestement. Car se il et tous ses
complisses en ce cas l’eussent iuré, (a nul n’en soit grief) il a
esté, est et sera moult de plus vaillans femmes plus
honnestes,
mieulx moriginees, et meismes plus sauans et dont plus
grant
bien est ensuiui au monde que oncques ne fist de sa
personne,
230 meismement en policie mondaine et en meurs vertueux tres
enseignees, et pluseurs qui ont esté cause de reconciliement
de
leurs maris et porté leurs affaires et leurs secrez et leurs
passions
doulcement [fol. 91 a] et secretement, non obstant leurs
fussent leurs maris rudes et malamoreux. De ce treuue l’en
235 assez preuues en la Bible, et es autres ancienes hystoires,
comme Sarra, Rebecha, Ester, Judic, et autres assez. Et
mesmes en noz aages auons veu en France moult de
vaillans
femmes, grans dames et aultres de noz dames de France: la
saincte deuote royne Jehanne, la royne Blanche, la duchece
240 d’Orliens, fille de roy de France, la duchece d’Aniou, qui ores
est nommee royne de Cecille, qui tant orent beauté,
chasteté,
honnesteté et sauoir, et autres assez. Et de mendres vaillans
preudefemmes comme Madame de la Ferté, femme messire
Pierre de Craon, qui moult fait a louer, et assez d’autres qui
245 trop seroit longue narracion dire plus.
Et ne croiez, cher sire, ne aucun autre n’ait oppinion que
je die ne mette en ordre ces dictes deffenses par excusacion
fauourable pour ce que femme suis. Car veritablement
mon motif n’est simplement fors soustenir pure verité, si
250 comme je la sçay de certaine science estre au contraire des
dictes choses de moy niees. Et de tant comme voirement
suis femme, plus puis tesmoingnier en ceste partie que cellui
qui n’en a l’experience, ains parle par deuinailles et
d’auenture.
Mais apres toutes ces choses, par amour soit consideré quel
255 est la fin du dit traictié; car si comme dit un prouerbe: “A la
fin son[t] terminees les choses,” si soit veu et notté a quoy
peut
estre profitable la treshorrible et honteuse conclusion, que
dis
ie honteuse, mais tant deshonneste que [fol. 91 b] je ose
dire
que personne aucune amant vertus et honnesteté ne l’orra,
260 qui tout ne soit confus de honte et abhominé d’ainsi ouir
discerner et desioindre et mettre soubz deshonnestes
ficcions,
ce que honte et raison doit reffraindre aux bien ordenez
seulement le penser. Encore plus i’ose dire que mesmes les
goliars aroient orreur de le lire ou ouir en publique, en
places
265 honnestes, et deuant personnes que ilz reputassent
vertueuses.
Et donc que fait a louer lecture qui n’osera estre leue ne
parlee
en propre fourme a la table des roines, des princeces, et des
vaillans preudefemmes, a qui conuendroit couurir la face
de honte rougie?
270 Et se tu le veulz excuser en disant que par maniere de
jolye nouuelle lui plot mettre la fin d’amours par telles
figures,
je te respons que en ce nulle estrangeté ne nous raconte; ne
scet on comment les hommes habitent aux femmes
naturelment?
Se il nous narrast comment ours ou lyons, ou oiseaux ou
275 autre estrange chose fust deuenus, ce seroit matiere de rire
pour la fable, mais nulle nouuelleté en ce ne nous annonce.
Et sans faille plus plaisantment et trop plus doulcement et
par
plus courtois termes s’en fust passé, et qui mieux plairoient
mesmes aux amans iolis et honnestes et a toute autre
vertueuse
280 personne.
Ainsi, selon ma petite capacité et foible iugement, sans
plus estre prolixe en langage, non obstant que assés plus
pourroit
estre dit et mieulx, ne sçay considerer aucune utilité ou
dit traictié. Mais tant m’i semble apperceuoir que grant
285 labeur [fol. 91 verso a] fu pris sans aucun preu, non obstant
que mon iugement confesse maistre Jehan de Meun moult
grant clerc soubtil et bien parlant; et trop milleur œuure plus
profitable et de sentement plus hault eust sceu mettre sus
s’il
s’y fust appliquié, dont fu dommage, mais ie suppose que la
290 grant charnalité peut estre, dont il fu remply, le fist plus
habonder a volenté que a bien proffitable, comme par les
operacions
communement sont cogneues les inclinacions. Non
obstant ce, ie ne repreuue mie le Romant de la Rose en
toutes
pars; car il y a de bonnes choses et de bien dictes sans
faille,
295 et de tant est plus grant le peril, car plus est adioustee foy
au
mal de tant comme le bien y est plus autentique. Et par ce
ont
mains soubtilz aucunesfois semees de grans erreurs par les
entremesler
et palier auec verité et vertus. Mais si comme dit son
prestre Genius: “Fuiez, fuiez femme, le mal serpent mucié
300 soubz l’erbe”, puis ie dire, fuiez, fuiez les malices couuertes
soubs ombre de bien et de vertu.
Pour ce dis en concluant a vous, sire treschier, et a tous

voz aliez qui tant le louez et si hault voulez magnifier que a
pou tous autres volumes presumés et osez abaissier deuant
lui,
305 n’est digne que louenge lui soit imputee (sauue vostre
bonne
grace) et grant tort faictes aux valables; car œuure sans
utilité et hors bien commun ou propre, poson[s] que elle soit
delictable, de grant labour et coust, ne fait a louer. Et
comme
anciennement les Romains triomphans n’atribuassent
louenge
310 aucune ne honneur a chose quelconques, se elle n’estoit a
l’utilité de la chose publique, regardons a [fol. 91 verso b.]
leur
exemplaire, se nous pourrons couronner cestui romant.
Mais je treuue, comme il me semble, ces dictes choses et
assez
d’autres considerees, que mieulx lui affiert enseuelissement
315 de feu que couronne de lorier, nonobstant que le claimez
miroir de bien viure, exemple de tous estaz de soy
politiquement
gouuerner et viure religieusement et sagement. Mais
au contraire (sauue vostre grace) je dis que c’est exortacion
de vice, confortant vie dissolue, doctrine pleine de
deceuance,
320 voye de dampnacion, diffameur publique, cause de
souspeçon
et mescreandise, honte de pluseurs personnes, et puet estre
d’erreur. Mais ie sçay bien que sur ce en l’excusant vous me
respondrez que le bien y est enorté pour le faire et le mal
pour l’eschiuer. Si vous puis souldre par meilleur raison que
325 nature humaine, qui de soy est encline a mal, n’a nul
besoing
que on lui ramentoiue le pié dont elle cloche pour plus droit
aler. Et quant a parler de tout le bien qui ou dit liure puet
estre noté; certes trop plus de vertueuses choses mieulx
dictes, plus autentiques et plus proffitables mesmes en
politiquement
330 viure et moralment sont trouuees en mains autres volumes,
fais de philosophes et docteurs de nostre foy comme
Aristote, Seneque, Saint Pol, Saint Augustin, et d’aultres (ce
sauez vous) qui plus valablement et plainement
tesmoingnent
et enseignent [suir] vertus et fuir vices que maistre Jehan de
335 Meun n’eust sceu faire. Mais si voulentiers ne sont veus ne
retenus communement des charnelz mondains, pour ce que
moult plaist au malade qui a grant soif, quant le medicin
octroye que il boiue fort et tout [fol. 92 a] voulentiers, pour
la
lecherie du boire se donne a croire que ia mal ne lui fera. Et
340 si me rens bien certaine que vous—a qui Dieu l’octroit et
tous
autres—par la grace de Dieu ramenez a clarté et purté de
nette
conscience, sans soilleure ou pollucion de pechié ne
entencion
de lui, nettoiez par poincture de contriction (laquelle euure
et
fait cler veoir le secret de conscience et condempne propre
345 voulenté), comme iuge de verité, ferez aultre iugement du
Romant
de la Rose, et vouldriez peut estre que oncques ne l’eussiez
veu. Si souffise atant. Et ne me soit imputé a folie,
arogance, ou presompcion d’oser moy femme reprendre et
redarguer
aucteur tant soubtil et son œuure amenuisier de
350 louenge, quant lui seul homme osa entreprendre a diffamer
et
blasmer sans excepcion tout un sexe.
ITEM—comme la dicte Christine eust enuoié la copie de

la
dicte epistre a maistre Gontier Col, lui renuoya l’epistre, qui
s’ensuit.
NOTES
[l. 1] (Superscription) L’epistre crestienne au preuost de Lisle enuoyé

par la dicte contre le romant de la Rose F.
(Souffisant, scauent) interverted A.
(prevost de Lisle) wanting C.
[l. 3] (monseigneur ... Lisle) wanting F.
[l. 4] (treschier sire) interverted F.
[l. 6] (Christine de Pizan) wanting F.
[l. 8] (aucunement) wanting F (inserted after despris).
[l. 11] (moy) preceded by et B.
[l. 12] (de voz ditz fait en reprenant) de voz diz fait en reprouuant B, de
voz diz faiz si comme il me semble en reprenant D, de voz diz fait
comme il me semble en reprenant E.
[l. 15] (icellui) wanting A.
[l. 16] (ayant) aie F.
(dicte) wanting C.
[l. 20] (clerc soubtil) wanting F.
(vostre dicte epistre) wanting F.
(s’adrece) preceded by il F.
[l. 21] (et soustenir) wanting D E.
(bonne) benigne C.
[l. 23] (puet) doit C D E.
[l. 26] (dit) wanting F.
[l. 28] (d’oser) wanting F.
(repudier) de reputer F.
[l. 29] (aucteur) acteur C D E.
[l. 32] (commandee) followed by si F.
[l. 33] (aprise) aprinse C.
[l. 34] (de belle) par belle A.
[l. 36] (ne) followed by l’an F.
[l. 39] (dit deuant) interverted C D E.
[l. 41] (accomplie) compilee D E, followed by et F.
[l. 42] (ou pis que oyseuse) wanting F.
[l. 44] (commune) comme A.
[l. 45] (m’ot) moult F.
(peu) petit A.
[l. 47] (Sceus) sco B soulz F.
(comprendre) entendre C D E.
(en aucunes pars n’estoit) interverted F.
[l. 48] (m’en) me F.
[l. 52] (d’autre) d’entre F.
[l. 53] (y) wanting C.
[l. 54] (parle) parler A B C D E F.
[l. 56] (first plus) wanting F.
(mesurez) amesures F.
[l. 58] (Mais en ... trop traicte) wanting F.
[l. 61] Cf. F. Michel, Roman de la Rose, t. I., p. 232.
[l. 63] (raisonnablement estre) interverted C.
[l. 69] (originel) et orgueil F.
[l. 70] (par comparaison) wanting A.
(puis alleguer) wanting F.
[l. 72] (fu) comes after pechié F.
[l. 73] (de soy, tres bel) interverted C.
[l. 77] (vous puis souldre) wanting F.
[l. 80] (deboutee) reboutee A B.
(en publique) wanting here, but follows hontoie F.
[l. 82] (et) de F.
[l. 86] (de) en F.
[l. 87] (nommees) nommeis F.
[l. 88] (la deshonnesteté de la chose) la chose deshonneste B.
[l. 94] (Et encore) encore F.
(me) wanting A.
(content) contampt F.
[l. 95] (1. de) wanting F.
[l. 99] (vrayement) vray amant F.
(ose) followed by bien F.
[l. 100] (celluy) ce F.
[l. 101] (autre) outre F.
(vaulsist) vaille F.
(s’ensuiuroit) s’ansieut F.
[l. 102] (fussent) soient F.
(Et) Parquoy F.
[l. 103] (par) en F.
[l. 104] (a royalment parler) a realment parler after contraire F.
(deceuoir) followed by car trop est pire le vice de propre malice
que cellui de simple ignorance A B.
[l. 110] (vilaine) villonie F.
[l. 112] (a) followed by maintenir F.
(vie honneste) interverted F.
(et querez) wanting C D E.
[l. 115] (ouir tant) interverted A B.
[l. 116] (pour Dieu) wanting F.
[l. 119] (bon) wanting F.
[l. 120] (ne entroduction) wanting F.
[l. 122] (qui) wanting A.
[l. 124] (ne peuent ... femmes) wanting F.
[l. 125] (en riens amenrir ne rendre empirees) ou riens amenrir ne rendre
empirees A, en riens amenrir ne riens empirer D, en riens amenrir ne
riens empirees E.
[l. 126] (Ha! Hay!) preceded by mais pourtant n’en puet de riens
empirier F.
(et quant) wanting F.
[l. 128] (peut retenir) peut y retenir C y peut retenir F.
(d’ycellui traictié) wanting F.
[l. 129] (proffitables) bons F.
(ouir) followed by et proufitables F.
[l. 130] (Mais) followed by que dit F.
(le personnage ... appelle) wanting F.
(dit merueilles) wanting F.
[l. 131] (doubte) faille C D E.
[l. 132] (Mais pour Dieu ... et de noms et) et moult voudroie auoir trouué,
qui bien me sceust souldre par quoy mon entendement fust rassadiés a
quoy peust estre proufitable tant de choses deshonnestes nommees. F.
[l. 137] (moz) preceded by ou clers et dit F.
[l. 138] (les quelz) desquelz deffaillir F.
(doiuent) doit F.
(teus et non nommez) sobrement parlé F.
[l. 139] (Et) wanting D E.
(puis que) dont on F.
(on) wanting A.
(l’œuure) followed by qui par l’ordre de nature ne puet faillir. Mais
ne say entendre ne aduiser que ramanteuoir et commander enfigmes
eluchans et plaisans aux charneulx ce que puet parnit tourner ad
inconveniant de pechié estre licite a dire. F.
[l. 143] (l’aucteur) wanting A.
[l. 144] (puis) followed by a. F.
[l. 145] (dit) wanting F.
(sermon) followed by quil impute a Genius F.
(maniere de) wanting F.
[l. 146] (qui la sont) wanting F.
(cellui) wanting F.
[l. 148] (ne en ce ne fait) il n’y F. Cf. Michel, op. cit. t. 2, p. 288, sqq.
[l. 152] (erreur) orreur B.
(Ha!) followed by dieux F.
(quel semence et) wanting F.
(semence) sentence C.
[l. 153] (doctrine) followed by ha! hay! quel semence F.
(en peuent ensuiuir) en sunt ensuiuis F.
(Je croy que ... enortement) Quans en sont devenus hermites et
entrés en religion ou eulx retrais de malle vie et esté sauués pour ce
saint ennortement F.
[l. 156] (et esté) et estre C D E.
[l. 157] (dire l’ose a qui) je l’ose bien dire F.
(a qui qu’il) a qui qu’il qu’il [sic] A.
[l. 159] (qui peut estre ... et pechié) Bien est vray que je condampne mie
l’acteur ou aucteurs en toutes pars dudit liure. Car ce ne pouroie faire
veritablement et de bonnes choses y a et bien dictes, et de tant est
plus grant peril comme le bien y est plus autentiquement dit. Car
mieulx autressy est ajoustees foy au mal. Et par ce ont mains soubtilz
aucune fois fammes de grans erreurs parlés entrammesler auec grans
vertus, verités et choses belles et bien dictes, ainsy comme dit le
personnaige qu’il appelle Genius la ou il moult ennorte que l’an
eschieue la malice et la male beste, famme, comme du froit serpant
mucié soubz l’erbe vert. Ainssy puet on dire que l’en se gard de
mauuaistié muciee soubz ombre de bien. F.
[l. 160] (Et encore pour Dieu) Et pour Dieu encore C.
(pour Dieu regardons oultre un petit) vuellons ung petit
resgarder F.
[l. 161] (a) followed by la F.
[l. 162] (et si) wanting F.
[l. 163] (de) et F.
[l. 165] (aucques) auecques F.
[l. 166] (me) wanting F.
[l. 167] (le) wanting F.
(comme passioné) wanting F.
[l. 170] (grans) wanting C.
[l. 172] (si) wanting F.
[l. 173] (Cy a ... commander a) Si se contre dit mallement quant il
commande F.
(a fuir ce que il veult que on suiue, et suiuir) wanting D E.
(suiuir) fuir F.
[l. 175] (mais) wanting F.
[l. 176] (aucunement) wanting F.
(inconuienent) la chaleur du feu F.
[l. 177] (eschiuer le doit) eslongnier s’en conuient F.
[l. 178] (est si engrant) tant est engrant doubte F.
(comme il recorde, dont) wanting F.
[l. 179] (ou) en F.
(trouua) pensa F.
[l. 180] (Mais) wanting F.
[l. 181] (pry) followed by a F.
(y adioustent foy) l’aprennent. F.
[l. 183] (mors) followed by ou F.
(ou reprochiez en rue par l’encusement de leurs femmes? Si croy)
par l’ancusement de leurs femmes ou reproches en rue. Je croy F.
[l. 184] (que) ce que B.
(semees) fammes F.
[l. 185] (obstant) followed by je confesse bien F.
(et louable que) d’ennorter pour toute seuretey F.
[l. 186] (tenist son secret ... plus seur) son secret celast F.
(car de toute ... de vicieux) car hommes ou fammes ne sont mie
tous bons F.
[l. 187] (et n’a pas moult comme ouy raconter que un) et n’a pas grant
temps que je oy raconter comment ung C, et n’a pas moult que ung F.
[l. 188] (puis) wanting F.
(soy estre descouuert) wanting F.
[l. 189] (en qui se fioit) a qui fiablement c’estoit descouvert F.
[l. 190] (pou vont) interverted C.
(de tant) des F.
(maulz) followed by et F.
[l. 192] (et secretement) wanting F.
[l. 193] (il n’appert a nullui) nul ne s’en appersoit F.
[l. 194] (comme autrefois ay) comme j’ay aultrefois F.
(sur ceste matiere) wanting F.
[l. 195] (dictié) traictié A.
(appellé ... d’Amours) wanting F.
[l. 196] (contrees ... royaumes) les royaumes, les contrees et les
empires F.
[l. 197] (Mais) Pour dieu mercy F.
(disons) wanting F.
[l. 198] (crismes) followed by les F.
(on) wanting C D E.
[l. 199] (faire) followed by ne C D E.
(de quoy te deçoiuent) wanting F.
[l. 200] (ou tollent elles pas) ne tollent mie C D, ou tollent mie E.
[l. 201] (elles) ilz F.
(mie) pas F.
[l. 202] (pas) mie A F.
[l. 203] (Bon) preceded by commen[t] de desoiuent elles F.
[l. 204] (sauoir) preceded by de F.
(comment ... deçoiuent) wanting F.
(encore) puis F.
(superfluement et) wanting F.
[l. 205] (des) de A.
[l. 206] (ne) n’en C D E.
(duquel estat ne pot par experience) de quoy il ne sceit riens F.
[l. 207] (tant en) si F.
(A quelle bonne fin ... ne quel bien) Quel bien en puet il F.
[l. 208] (ensuiure) s’ensuiuir C.
(ne quel bien ensuiure) et quel bien ensuiure A quel bien
ensuiure B.
(n’y sçay entendre) wanting F.
[l. 209] (empeschement de ... de mariage, et) wanting F.
[l. 210] (tant) followed by de fatras F.
(babuises) preceded by de A D, wanting F.
(y) n’y B.
(et fatras se foy y adioustent) wanting F.
[l. 211] (Dieux) Ha F.
[l. 212] (proffitable) cause de grant bien F.
(Mais) followed by aultre ne le say entendre fors que sans cause
prist grant peinne Et F.
(puisque en general) ce que generalment C.
[l. 213] (toutes) followed by les F.
[l. 214] (acointance) followed by Je ne tieng que onques fuste acointe F.
(hantise) hantast F.
(de femme) a famme C.
[l. 215] (ne vertueuse) wanting F.
(pluseurs) followed by paillardes et F.
[l. 216] (et de male vie) wanting F.
(comme font ... luxurieux) comme sont celles qui ou vilain vice de
luxure trop communement s’abandonnent F.
[l. 217] (toutes) followed by femmes F.
[l. 219] (les deshonestes ... elles fuir) les femmes ou sont les grans et
honteux vices comme les dissolues et celles conseiller a non suir F.
[l. 220] (et iuste) wanting F.
(non, ains sans excepcion ... contraire appere manifestement) il
n’execte riens, tout est d’ung commun ordre a son dit F.
[l. 224] (qui) que A.
[l. 225] (Car) Mais sans faille F.
[l. 226] (il a esté) ja a esté D E.
[l. 227] (vaillans) valables A B, de trop plus vaillans F.
[l. 229] (que oncques ne fist de sa personne, meismement) que il
oncques ne fu meismes en pollicie mondaine F.
[l. 230] (et en meurs ... pluseurs) wanting F.
[l. 231] (ont esté cause) cause ont esté F.
(1. de) du A F.
[l. 232] (leurs affaires et leurs secres et leurs passions B D E, leur affaires
et secres et leurs passions A, leurs passions C, leurs affaires et leurs
secres F.
[l. 233] (et) wanting F.
[l. 234] (maris) followed by moult F.
(malamoreux. De ce ... es autres) wanting F.
[l. 235] (anciennes hystoires) es anciennes hystoires on treuue l’en
asses. F.
[l. 236] (Sarra) followed by & A.
(Ester) wanting A.
(assez) followed by en aultres lieux F.
[l. 237] (mesmes) mesmement F.
(moult de vaillans femmes ... saincte deuote) de nos grans
dames F.
[l. 238] (et aultres de noz dames) wanting D E.
[l. 239] (royne Jehanne) la royne Jehanne, la sainte dame F.
(la duchece) madame la duchece F.
[l. 240] (la duchece) celle F.
[l. 241] (nommee) wanting F.
(tant orent ... et sauoir) tant ont esté belles, bonnes, saiges, et
honnestes. F.
(orent) eurent C.
(beauté) de beauté D.
[l. 242] (Et de mendres vaillans preudefemmes) de mendres vaillans
femmes C vaillans preudesfames F.
[l. 243] (femme) femme de F.
(qui moult fait a louer) wanting F.
[l. 244] (assez d’autres) et aultres assez A et moult d’autres C.
(assez d’autres) asses d’autres. Et se largement a parlé nul blasme
ne doit par raison estre imputé aux fammes, mais a celluy, qui si a dit
la mensonge loing de apparance de verité que elle n’est creable et ne
croye nul. F.
(qui trop seroit longue narracion ... ordre ces dictes) wanting F.
[l. 247] (ne) ou A.
(deffenses par excusacion fauourable) que ceste deffence ou
excusacion d’ye par faueur ne y ua uiuement F.
[l. 248] (Car veritablement mon motif n’est simplement fors soustenir) Car
sans faulte n’est la cause fors pour soustenir F.
[l. 249] (si) wanting F.
[l. 250] (au contraire ... Et de) wanting F.
[l. 251] (comme voirement suis) comme je suis voirement, F.
[l. 252] (plus) plus veritablement F.
(en ceste) wanting F.
(partie) wanting F.
(cellui) cil F.
[l. 253] (n’en) wanting F.
(l’experience ... d’auenture) l’auenture parle F.
[l. 254] (par amours soit consideré) regardons. F.
[l. 255] (la fin) la fin la fin [sic] F.
(du dit traictié; car) wanting F.
(dit) recorde F.
[l. 256] (terminees) followed by et cogneues F.
(si soit veu ... deshonneste) Pour Dieu que j’apraingne que puet
estre valable ordre profitable et tresabhominable et honteuse
conclusion dis ie deshonneste, voire F.
[l. 257] (que dis ie honteuse mais) wanting C.
[l. 258] (deshonneste) deshonteuse A.
[l. 259] (personne aucune amant ... ce que honte) repeated B.
[l. 260] (et abhominé d’ainsi ouir ... ce que honte) d’ainsy oir, discerner, et
desioindre et mettre en honteux termes ce que honte F.
[l. 262] (honte et raison) raison et honte B D E.
[l. 263] (le penser) de penser C les pensees F.
(Encore plus ... reputassent vertueuses) wanting F.
[l. 266] (donc) pour Dieu F.
(parlee) ramenteué F.
[l. 270] (Et se tu le veulz ... raconte) quel bien donques y puet on
glosser F.
[l. 272] (raconte) followed by ne aprent A B.
[l. 273] (les) wanting F.
[l. 274] (Se il nous narrast comment) Quel estrange auenture est ce. Et ce
dit eust que deuenus fust F.
(oiseaux) oysel F.
[l. 275] (autre estrange chose) autre chose A autre chose estrange B.
(matiere) de matiere B.
(autre ... ne nous annonce) beste estrange. Sur ce point oultre le
commun cours, bon seroit l’oyr pour la merueille. Mais se dire voules
que n’eust esté au propos de sa matere quil tendoit aperceuir et
concluire la fin d’amours entrés trop. F.
[l. 277] (et sans faille) wanting F.
(doulcement et) followed by plus gracieusement F.
[l. 279] (mesmes) mesmement C.
(mieulx) wanting F. [Transcriber's note: the word mieux appears in line
278, the word mieulx in line 283.]
[l. 281] (Ainsi selon ma petite ... cogneues les inclinacions) wanting F.
[l. 285] (sans aucun preu) sans grant preu A.
[l. 285-301] (Non obstant ce ie ... de bien et de vertu) Bien est vray que je
condampne mie l’acteur ou aucteurs en toutes par dudit liure. Car ce
ne pouroie faire veritablement; et de bonnes choses y a et bien dictes
et de tant est plus grant peril comme le bien y est plus autentiquement
dit. Car mieulx autressy est ajoustees foy au mal. Et par ce ont mains
soubtilz aucune fois fammes de grans erreurs parlés entrammesler
auec grans vertus, verités et choses belles et bien dictes ainsy comme
dit le personnaige qu’il appelle Genius la ou il moult ennorte que l’an
eschieue la malice et la male beste famme comme du froit serpant
mucié soubz l’erbe vert. Ainssy puet on dire que l’en se gard de
mauuaistié muciee soubz ombre de bien. F.
[l. 292] (communement sont cogneues) sont communement cogneues C.
[l. 294] (de bien) bien A.
[l. 296] (par ce ont mains soubtilz aucunefois) pour ce pluseurs subtilz ont
aucunement C.
[l. 302] (dis en concluant a vous) wanting F.
[l. 303] (vos aliez) autres F.
(le louez, et si hault le voulez magnifier) le recommandes, loues,
magnifies, et si hault le voules asseoir F.
[l. 304] (presumés) voulez C D E.
(deuant lui; n’est digne ... couronne de lorier) wanting F.
[l. 314] (mieulx lui affiert) lui affiert mieulx C.
[l. 315] (nonobstant) preceded by Je dy certainement et en confirmant
mon oppinion que cestuy rommant dit de la Rose F.
[l. 316] (bien) bon B.
[l. 317] (et sagement) wanting A.
(Mais au contraire) que F.
[l. 318] (je dis que c’est) ains est F.
[l. 320] (voye) voire F.
(dampnacion) followed by erreur peruerse F.
[l. 321] (honte) preceded by voye et cause de dampnacion et F.
[l. 322] (Mais ie sçay ... vous me respondrez) Et ce pourtant excuser le
voules F.
[l. 323] (est ennorté) soit F.
[l. 324] (l’eschiuer. Si vous puis souldre par meilleur raison que nature
humaine, qui de soy est encline) soy garder. Je respons que humaine
nature, qui a mal est encliné de sa nature, F.
[l. 326] (le pié) ce piet F.
[l. 327] (de tout le bien) des biens F.
(qui) que C.
(qui ou dit liure ... plus autentiques et) qui y sont trop de plus
grans biens F.
[l. 330] (autres) wanting F.
[l. 331] (docteurs) followed by autentiques F.
[l. 332] (Seneque) wanting F.
(Pol) Poul, et F.
[l. 333] (sauez vous) interverted F.
[l. 334] (et enseignent) suir F.
(que maistre Jehan de Meun n’eust sceu faire) wanting F.
[l. 336] (communement) wanting here, but follows mondains F.
(charnelz) wanting F.
[l. 338] (octroye que il boiue fort et) octroie a boire fort et C octroye qu’il
boiue fort et que B D.
(tout) wanting F.
[l. 339] (Et si me rens bien certaine) Encor dis et soustiens F.
[l. 340] (Dieu) wanting here, but comes before par F.
[l. 341] (Dieu) luy F.
(a) a la F.
(nette conscience) interverted F.
[l. 342] (ou) ne F.
[l. 343] (nettoiez) wanting F.
(laquelle) netoyes qui F.
[l. 345] (iuge) droit iuge F.
(du) dudit F.
[l. 347] (Si souffise atant) followed by Et que si grant louenge comme
vous imputes a luy (sauue vostre bonne grace) m’est aduis que grant
tort faites aux plus vallables; car œuure sans grant utilité du bien
commun ou propres en fait ou en exemple et on n’a fors seulement
delectacion et solas sans cause d’autre bien tout soit elle de grant
coust ou travail ne doit estre louee n’euxaussité, F.
[l. 348] (d’oser) d’ainsy oser, F.
(moy femme) wanting F.
[l. 349] (et) wanting F.
[l. 350] (quant lui seul homme] quant il qui fu seul homme F.
(entreprendre) wanting F.
[l. 351] (excepcion) exercitacion B.
(sans excepcion tout un sexe) interverted F.
[l. 352] (Item—comme la dicte Christine ... qui s’ensuit) wanting F.
[l. 353] (maistre Gontier Col) maistre gol [sic] A.
(renuoya) enuoyé B.
(qui s’ensuit) qui cy apres s’ensuit C.
[30] Ms. A (bib. nat. 835) is followed for orthography. The text is
determined by a comparison of A + B, C, D + E, variant readings being
noted. Except in rare cases which seemed specially interesting,
orthographical variants are not noted.
[31] Cf. Michel, op. cit., t. I., 145, 6.
[32] Cf. for idea of the “Roi, qui ne ment,” T. A. Jenkins, Longer French
Poems pp. 13, 143.
[33] Cf. Michel, op. cit, t. 2, p. 190 and Virgil, Bucolica, III. Eclogue, v.
92. Qui legitis flores et humi nascentia fraga, Frigidus, O pueri, fugite
hinc, latet anguis in herba.
[34] Michel, op. cit, t. 2, p. 182.
[35] Cf. M. Roy: Oeuvres poétiques de Christine de Pisan (in the Soc.
des anc. textes franç.) t. II, p. 21 l. 650.
V.
GONTIER COL TO CHRISTINE, ASKING FOR A COPY OF NO.
IV.
Maistre Gontier Col
A prudent, honnouree et sauent damoiselle Christine.
Femme de hault et esleué entendement, digne d’onneur
et
recommendacions grans, j’ay ouy parler par la bouche de
5 pluseurs notables clers que entre tes aultres estudes et
euures
vertueuses moult a louer, comme ie entens par leur
relacion,
tu as nouuellement escript par maniere de inuectiue
aucunement
contre ce que mon maistre, enseigneur et familier feu
maistre Jehan de Meun, vray catholique, solennel maistre,
et
10 docteur en son temps en saincte theologie, philosophe
tresperfont
et excellent, sachant tout ce qui a entendement humain
est scible, duquel la gloire et renommee vit et viura
es aages a venir [fol. 88 b] entre les entendemens par ses
merites
leuez par grace de dieu et euure de nature, fist et compila
15 ou liure de la Rose. Et comme dient les relateurs ou
refferendaires de ceste chose, t’efforces et estudies de le
reprendre
et chargier de faultes en ta dicte œuure nouuelle,
laquelle chose me vient a grant admiracion et merueille
inextimable,
et ad ce non croire me meut l’experience et exercite
20 de toy d’auoir sceu, leu, et entendu lui ou dit liure, et en
ses
autres fais en francois, et autres pluseurs et diuers
docteurs,
aucteurs, et poetes. Et pour ce que les denunciateurs de
ceste
chose tiennent et gardent, les aucuns par auenture
comme
enuieux sur les fais du dit feu maistre Jehan, ta dicte
inuectiue
25 comme chose singuliere et haultement composee, edefiee
et
conduicte a leur plaisir et intencion, si que de eulx n’en
puis
auoir copie ne original, te pry et requier sur l’amour que
tu as
a science que ta dicte œuure, telle que elle est, me
vueilles
enuoier par cest mien message ou autre tel comme il te
plaira,
30 afin que sur ce je puisse labourer et moy emploier a
soustenir
mon maistre et ses fais, dont il ne fust ia besoing que
moy ne
autre mortel s’en meslast s’il fust en vie, laquelle mieulx
ameroie auoir esté en mon temps que estre empereur des
Romains
presentement. Et pour toy ramener a vraie verité et
35 que plus auant saches et cognoisses les fais du dit de
Meun;
pour toy donner matiere de plus escripre contre lui, se
bon te
semble, ou a tes [fol. 88 verso a] satalices [read
satellites], qui en
ce fait t’ont boutee, pour ce que touchier n’y osoient ou
ne
sauoient, mais de toy veulent faire chappe a pluye; pour
dire
40 que plus y sauroient que une femme et plus reprimer la
renommee
(indeficient entre les mortelz) d’un tel homme,
t’enuoie patentement et hastiuement un pou de tresor[36]
que il
compila pour estre de ses enuieux et de aultres congneu
a sa
mort; lequel est incorrect par faulte d’escripuain, qui pas
ne
45 l’entendi comme il y pert, et n’ay eu espace ne loisir de le
veoir
ne corrigier au long pour la haste et ardeur que j’ay de
veoir
ton dessusdit œuure, et mesmement qu’il est a supposer
que bien sçaras les fautes de l’escripuain en ceste
compilacion
corrigier et entendre. Et quant ad ce qu’il fist du liure de
la
50 rose, ou plus a lettres et sentences estranges et diuerses,
l’as
voulu ou osé chargier, corrigier et reprendre comme ilz
dient,
une chose ne vueil oublier ne passer soubz dissimulacion:
que
se de ce ne te rappelles et desdis, je, confiant de bonne
et vraye
iustice et que verité (qui ne quiert angles) sera o moy,
combien
55 que en grans autres occupacions soye de present astraint
et aye esté le temps passé, entreprendray le soustenir
contre
tes autres escrips quelconques.
Escript hastiuement, presens maistres Jehan de Quatre
Mares, Jehan Porchier, conseilliers, et Guillaume de
Neauuille,
60 secretaire du roy nostre sire, le mardi XIII. jour de
septembre,
l’an mil et un.
Le tien, tant comme loy d’amistié puet souffire—Gontier
Col, secretaire du roy nostre sire.
NOTES
[l. 1] (Ms. A) (Maistre Gontier Col) wanting C D E.

[l. 2] (Christine) followed by de Pizan D.
[l. 8] (enseigneur) et seigneur C.
[l. 11] (et excellent) wanting D.
[l. 13] (entre) contre D.
(entendemens) enseignemens C.
[l. 16] (le) la A C.
[l. 24] (Jehan) followed by de Meun A B.
[l. 32] (mieulx ameroie) ameroie mieulx B.
[l. 44] (pas) point A.
[l. 47] (mesmement) followed by qu’il est a supposer B.
[l. 48] (en ceste compilacion) wanting A.
(en ceste) corriger brieue B.
[l. 49] (ad ce) en ce A a ce C.
[l. 54] (o) auec C.
[l. 57] (tes) followed by a faint mark above, which resembles the
abbreviation of ‘et.’
[l. 58] (maistres) maistre A, wanting B.
[36] Cf. Le Trésor de maistre Jehan de Meung ou les Septs Articles

de la Foi, Méon, Roman de la Rose, t. 3, p. 331.
VI.
GONTIER COL TO CHRISTINE, REPROVING HER FOR HER
ATTITUDE TOWARDS THE ROMAN DE LA ROSE.
Maistre Gontier Col.

A femme de hault entendement damoyselle
Christine.
Pour ce que la diuine escripture nous enseingne et
comande
que quant on voit son ami errer ou faire faulte, on le doit
5 corrigier et reprendre premierement a part, et se il ne se
veult amender pour celle fois, que on le corrige deuant
gent;
et se pour ce ne se veult corrigier, que on le tiengne
tanquam
eunucus[37] et publicanus, et je te aime loyaument pour
tes [fol.
92 b] vertus et merites, t’ay premierement par une
mienne
10 lettre, que auant yer t’enuoyay, exortee, auisee, et priee
de
toy corrigier et amender de l’erreur manifeste, folie ou
demenance
trop grant a toy venue par presompcion ou oultrecuidance
et comme femme passionnee en ceste matiere—ne te
desplaise se ie dy voir. Je ensuiuant le commandement
diuin
15 ayant de toy compassion par amour charitable te pry,
conseille
et requier la seconde fois par ceste moye cedule que ton
dessusdit erreur tu vueilles corrigier, desdire et amender
enuers le tresexcellent et irreprehensible docteur en
saincte
diuine escripture, hault philosophe et en toutes les sept
ars
20 liberaux, clerc tresperfont, que si orriblement oses et
presumes
corrigier et reprendre a sa grant charge et aussi enuers
ses
vrais et loyaulz disciples Monseigneur le preuost de Lysle
et moy et aultres, et confesser ton erreur. Et nous arons
pitié de toy et te prendrons a mercy en te baillant
penitence
25 salutaire. Et de ce auec la response de mon aultre lettre
te
plaise moy ta bonne voulenté faire sauoir a ton aise et
loisir,
auant que ie me mette en peine d’escripre encontre tes
faulses
(sauue ta reuerence) escriptures, que de lui tu as voulu
escripre.
Et se ores et aultreffois, quant ie te escripray, te appelle
en singulier,
30 ne te desplaise, ne le me imputes a arogance ou orgueil,
car c’est et a esté tousiours ma maniere, quant j’ay
escript a
mes amis, especialment quant sont lettrés. Dieux vuelle
briefment ramener ton cuer et entendement a vraye
lumiere
et cognoiscence de verité, car ce seroit dommage se plus
demouroies
35 en tel erreur soubz les tenebres [fol. 92 verso a]
d’ignorance. Escript ce jeudi XV iour de septembre.
le tien Gontier Col.
Cy apres s’ensuit la response enuoyee au dit maistre

Gontier
Col.
NOTES
[l. 1] Ms. A.
[l. 6] (pour) a C.
[l. 8] (et je) et pour ce que je C.

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Organic Chemistry 8th Edition William H. Brown

Organic chemistry William Henry Brown

Organic Chemistry 5th Edition Maitland Jones Jr.

Music Fundamentals A Balanced Approach Third Edition Sumy

The Art of Asking Questions 7th Edition Stanley Le Baron

The Systemic Turn in Human and Natural Sciences: A Rock in

MCQs for the FRCS(Urol) and Postgraduate Urology

Britain by the Book A Curious Tour of Our Literary

This book is printed on acid-free paper.

Printed in the United States of America.

William H. Brown is Professor Emeritus at Beloit College, where he was twice

Thomas Poon is Professor of Chemistry in the W.M. Keck Science Department of

01 Covalent Bonding and

02 Acids and Bases 41

03 Alkanes and Cycloalkanes 63

04 Alkenes and Alkynes 108

05 Reactions of Alkenes and Alkynes 129

06 Chirality: The Handedness

08 Alcohols, Ethers, and Thiols 239

09 Benzene and Its Derivatives 282

01 Covalent Bonding and Summary of Key Questions 57

02 Acids and Bases 41 and Cycloalkanes? 87

2.2 What Are Brønsted–Lowry Acids and Quick Quiz 96

04 Alkenes and Alkynes 108 Looking Ahead 165

How Are Haloalkanes Named? 201

7.3 What Are the Products of Nucleophilic C H E MI C AL C O NN E C T I O NS

What Are Alcohols? 240

13 Carboxylic Acids 457

13.4 What Are the Acid–Base Properties C H E MI C AL C O NN E C T I O NS

Quick Quiz 480 14E Systematic Acquired Resistance in Plants 506

Key Reactions 480

14.2 What Are the Characteristic Reactions of Problems 556

Key Reactions 582 18.6 What Are the Three-Dimensional Shapes

What Are Carbohydrates?

Summary of Key Questions 606 19.5 What Are Prostaglandins? 662

Quick Quiz 608 19.6 What Are Fat-Soluble Vitamins? 665

Key Reactions 608 Summary of Key Questions 668

Problems 609 Quick Quiz 669

Looking Ahead 614 Problems 669

Group Learning Activities 614 Looking Ahead 672

Putting It Together 615 Group Learning Activities 673

17A Relative Sweetness of Carbohydrate 19A Snake Venom Phospholipases 657

18 Amino Acids and

What Are Nucleosides and

18.1 What Are the Many Functions of Nucleotides? 675

Appendix 1  cid Ionization Constants

21.3 What Are the Ten Reactions of Glossary G.1

Goals of This Text

CH3CH “ CHCH 3 + H ¬ Cl CH3C H ¬ CHCH3 + Cl

(a nucleophile) (an electrophile) sec-Butyl cation

curved arrows used in a mechanism are H +

a bond or from an unshared electron pair

a common mistake is to use curved arrows to indicate

See problems 5.19, 5.20, 5.28, 5.32

this carbon forms the

CH3 CH3 CH3

CH3 CH3 CH3

Appendix 1 cid Ionization Constants